First Date with a Ladyboy

Posted on July 19, 2019
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Are you going out on a date with a ladyboy for the very first time?  Are your nerves unstoppable and your neurons have left the building?  Calm down Bruce, I will help you find a way in dealing with your first date with a ladyboy.

I’m a ladyboy myself and if that’s not enough to pacify your anxiety, I don’t know what will.  Please take these tips with a grain of salt because we all have different individualities.  Way to contradict yourself there Amanda.  Before you judge me, hear me out lol.  I’m assuming that you’re going out on a date with a transgender woman from Asia because you’re in an article which uses the ladyboy term that is widely used in the east.  I’m from the Philippines and I’m going to share with you 3 key topics that are of paramount importance in most Asian women’s lives.


I cannot stress enough of how important it is for you to be family-oriented when you’re dating an Asian ladyboy.  We, most of the time, put our family, most especially our parents, above ourselves.  If you’re going to be dating a ladyboy from Asia, you have to be prepared to love her mother, father, brother, sister, and down to her very last 3rd cousin if you want the relationship to work.  It’s inevitable that you’ll be invited to tag along with your future ladyboy girlfriend in family affairs so once you’re in your romantic date, you have to let her know verbally that family ties matter.


I’m not saying that western people are all in an open relationship so please don’t attack me.  It’s just that from my experience, most of the American guys I’ve dated are more than willing to exercise their infidelity.  Monogamy is not reaching for the stars and if you’re looking of turning your ladyboy date into a wife, you have to have a strong stance with this issue.  Tell her that you’re not into threesomes and cheating and you want a love that’s only exclusive for 2 that’s hopefully going to last a lifetime.  Not only will she be smitten, but she might also be able to feel love at first sight.  Remember, your goal is not only to leave her besotted, but you must also beguile her.

Pay for the damn bill

I’m a very independent woman but if you’re not going to foot the bill on the first date which YOU invited me on, I will play TLC’s “No Scrubs” in full volume while we’re in a quaint restaurant while taking the cash out of my wallet.  This is pretty much common sense but I’m just here to remind you that this behavior isn’t cute.  Even if the date didn’t turn out well, still pay for the bill you jerk.  Anyway, these are just a few things of what you must remember when you’re on the first date with a ladyboy.

Have a great time and remember to not get too drunk. Keep yourself together Bobby.



About the author

Just a random ladyboy playing with makeup and skincare. Loves bacon and the operating table. I also write at

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